Trimethyl orthoformate → 6-(1H-benzimidazol-1-yl)-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[C:11]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)[CH:10]=1.[CH:29](OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[N:8]1([C:9]2[N:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[C:11]([NH:19][CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=3)[CH:10]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[CH:29]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
9 mg of 6-[(2-aminophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of step 1 of Example 365) was suspended in 0.2 ml of methanol, to which 0.2 mL of trimethyl orthoformate and a catalytic amount of p-toluenesulfonic acid monohydrate were added at room temperature, and stirred at the same temperature for 4 hours. The solvent was evaporated, saturated sodium bicarbonate was added to the residue, extracted with chloroform, the extract was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 9 mg (yield 94%) of the title compound as a light brown solid.
Workup
- customThe solvent was evaporated
- additionsaturated sodium bicarbonate was added to the residue
- extractionextracted with chloroform
- washthe extract was washed with water
- dry with materialdried on anhydrous sodium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-7ddf0498917045ffaba8f398893ef18f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575153B2
Reaction notes
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